4-Methoxybenzylamine → (4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-yl]-amine

HRID 2237922Notes

Reaction equation

HRID 2237922 reaction equation
Br[C:2]1[N:3]=[N:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CCN(C(C)C)C(C)C.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1>CCO>[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:2]2[N:3]=[N:4][C:5]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[CH:6][C:7]=2[C:8]([F:11])([F:10])[F:9])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 866080213-Bromo-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazine

Product 1

HCID 86608020(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-yl]-amineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazine (example C.26 step 7) (5.76 g, 16 mmol), DIPEA (3.19 mL, 19 mmol) and 4-methoxybenzylamine (2.4 mL, 19 mmol) in EtOH (25 mL) was refluxed for 18 h under argon atmosphere. Cooled to 23 C, the mixture was poured onto water, the precipitated solid was filtered off, washed with water and dried in air at 60° C. on the heating plate to give the title compound as an off-white solid (6.49 g, 98%). MS (ISP) 428.3 [(M+H)+]; mp 101-103° C.

Workup

  1. temperaturewas refluxed for 18 h under argon atmosphere
  2. temperatureCooled to 23 C
  3. additionthe mixture was poured onto water
  4. filtrationthe precipitated solid was filtered off
  5. washwashed with water
  6. customdried in air at 60° C. on the heating plate

Sources & evidence

ORD record
ord-e1efb76ac4134f8c9e4bcbceb9d97136
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

Loading…